EP0612831B1 - Flammfestes Hydrauliköl - Google Patents

Flammfestes Hydrauliköl Download PDF

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Publication number
EP0612831B1
EP0612831B1 EP93119558A EP93119558A EP0612831B1 EP 0612831 B1 EP0612831 B1 EP 0612831B1 EP 93119558 A EP93119558 A EP 93119558A EP 93119558 A EP93119558 A EP 93119558A EP 0612831 B1 EP0612831 B1 EP 0612831B1
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EP
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Prior art keywords
acid
flame retardant
hydraulic oil
set forth
retardant hydraulic
Prior art date
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Expired - Lifetime
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EP93119558A
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English (en)
French (fr)
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EP0612831A1 (de
Inventor
Kazuaki C/O Idemitsu Kosan Co. Ltd. Abe
Hiromichi C/O Idemitsu Kosan Co. Ltd. Seiki
Mitsuhiro C/O Idemitsu Kosan Co. Ltd. Iwata
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Idemitsu Kosan Co Ltd
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Idemitsu Kosan Co Ltd
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    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/043—Ammonium or amine salts thereof
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    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
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    • C10M2223/045—Metal containing thio derivatives
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    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/02—Esters of silicic acids
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/041—Siloxanes with specific structure containing aliphatic substituents
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    • C10N2010/04—Groups 2 or 12
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10N2040/02—Bearings
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/06—Instruments or other precision apparatus, e.g. damping fluids
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    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids
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    • C10N2040/30—Refrigerators lubricants or compressors lubricants
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    • C10N2040/32—Wires, ropes or cables lubricants
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    • C10N2040/34—Lubricating-sealants
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    • C10N2040/38—Conveyors or chain belts
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/40—Generators or electric motors in oil or gas winning field
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/42—Flashing oils or marking oils
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/44—Super vacuum or supercritical use
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/50—Medical uses

Definitions

  • the present invention relates to a flame retardant hydraulic oil to be used in rolling mills, die casting machines and the like in the field of the steel making industry and the nonferrous metal industry and in hydraulic instruments and the like in the construction industry. More particularly, it relates to a flame retardant hydraulic oil excellent in the flame retardancy, heat stability and oxidative stability, unaccompanied by the dangers of pinhole fire at sites of use and giving rise to no environmental contamination.
  • the flame retardant hydraulic oils have the following characteristics:
  • hydraulic oils of emulsion series and those of water-glycol series are short on their heat stability, oxidative stability, lubricity or accompanied by the difficulty to dispose of waste water.
  • hydraulic oils of phosphoric acid ester series have the shortcomings that their viscosity-temperature properties and hydrolytic resistance are deficient, they are responsible for the deterioration of seal materials and the exfoliation of coats and it is difficult to dispose of waste oils by burning.
  • GB-A-2 063 909 discloses a hydraulic fluid comprises a blend of 50 ⁇ 97% of an oleic acid ester of a polyol, 3 ⁇ 50% of a mixture of polyols and branched unsaturated C 12-20 fatty acids, 0.01 ⁇ 2% of a phenolic antioxidant, 0.01 ⁇ 2% of a diphenyl amine antioxidant, and 1 ⁇ 1000 ppm each of (I) a mixture of a fatty acid partial ester, aliphatic hydrocarbon and silica and (II) a mixture of metal soaps in a hydrocarbon oil, as defoamants.
  • flame retardant hydraulic oils disclosed in said patent applications have the flame retardancy defined only in terms of flash point.
  • the most important problem of flame retardant hydraulic oils is accidents to be caused by pinhole fire.
  • the flame retardant hydraulic oils should have the properties that they are hard to catch fire even if they are erupted from pinholes and, even in the case of catching fire, do not permit it to develop into the continuous burning if the source of fire is removed. These properties cannot be obtained merely by having the high flash points.
  • the present inventors have taken note of said properties of continuous burning and conducted the studies by spraying and burning various flame retardant oils under high pressure.
  • the studies have resulted in an outcome that conventional flame retardant oils of fatty acid ester series (particularly the fatty acid esters made of the oleic acid only) don't have the sufficiently satisfactory flame retardancy, although they are highly spoken of as flame retardant.
  • the present inventors have made the further intensive studies with a view to developing a flame retardant hydraulic oil of fatty acid ester series free from the properties of continuous burning and excellent in the heat stability, oxidative stability and fluidity.
  • the desired flame retardant hydraulic oil can be obtained by incorporating a fatty acid ester which is formed by reacting a specific polyol with an oleic acid and a isostearic acid or with the oleic acid, the isostearic acid and another monocarboxylic acid in a specific ratio.
  • the present invention has been completed on the basis of this finding.
  • an object of the present invention is to provide a flame retardant hydraulic oil containing a hydraulic base oil consisting essentially of a synthetic ester, which is a product formed by reacting (A) at least one polyol selected from the group consisting of neopentyl glycol, 2,2-dimethyl-3-hydroxypropyl-2', 2' -dimethyl-3'-hydroxypropionate, and trimethylolpropane with (B) a carboxylic acid comprising 15 to 85% by mole of oleic acid based on the total carboxylic acid and 15 to 85% by mole of isostearic acid based on the total carboxylic acid or a carboxylic acid obtained by incorporating into said carboxyli acid 70% by mole or less of monocarboxylic acid having 6 to 22 carbon atoms (provided that the oleic acids and isostearic acids are excluded) based on the total carboxylic acid, said synthetic ester having a kinematic viscosity of 40 to 80
  • the flame retardant hydraulic oils of the present invention use a hydraulic base oil comprising a fatty acid ester as the essential component.
  • the fatty acid esters of the present invention are a synthetic ester obtained by reacting a polyol of Component (A) with an oleic acid and an isostearic acid of Component (B), or by reacting a polyol of Component (A) with an oleic acid, isostearic acid and a monocarboxylic acid having 6 to 22 carbon atoms (provided that oleic acids and isostearic acids are excluded) of Component (B).
  • the polyols of Component (A), which are used in the reaction to form the synthetic esters are at least one polyol selected from the group consisting of neopentyl glycol, 2,2-dimethyl-3-hydroxypropyl-2', 2'-dimethyl-3'-hydroxypropionate, and trimethylolpropane. These polyols can be used singly or in their two or more mixture.
  • the carboxylic acids of Component (B) which are used in the reaction to form the synthetic esters are a carboxylic acid comprising an oleic acid and an isostearic acid as the essential component and further preferably a monocarboxylic acid having 6 to 22 carbon atoms, provided that the oleic acids and isostearic acids are excluded.
  • the carboxylic acids of Component (B) comprise the oleic acids in a ratio of 15 to 85% by mole to the total carboxylic acid, the isostearic acid in a ratio of 15 to 85% by mole to the total carboxylic acid and the monocarboxylic acid having 6 to 22 carbon atoms in a ratio of 70% by mole or less to the total carboxylic acid, if said monocarboxylic acids are put to use.
  • the ratio of the oleic acids in the carboxylic acids is less than 15% by mole, the low fluidity would undesirably result. If it is more than 85% by mole, the flame retardancy would be undesirably deficient. Furthermore, if the ratio of the isostearic acids is less than 15% by mole, the flame retardancy would be undesirably deficient. If it is more than 85% by mole, the fluidity would be undesirably at a low side.
  • the monocarboxylic acids having 6 to 22 carbon atoms are not particularly limited. Their examples include a straight chain saturated fatty acid such as caproic acid, enanthic acid, caprylic acid, pelargonic acid, capric acid, undecanoic acid, lauric acid, tridecanoic acid, myristic acid, pentadecanoic acid, palmitic acid, heptadecanoic acid, stearic acid, nonadecanoic acid, arachic acid and behenic acid; a straight chain unsaturated fatty acid such as undecenoic acid, elaidic acid, cetoleic acid, erucic acid and brassidic acid; and a branched chain saturated fatty acid such as isomyristic acid, isopalmitic acid, 2,2-dimethylbutanoic acid, 2,2-dimethylpentanoic acid, 2,2-dimethyloctanoic acid, 2-ethyl-2,3,3-trimethylbutanoic acid
  • the hydraulic base oils comprise as the essential component the synthetic esters formed by the ordinary esterification or the transesterification of polyols of Component (A) to carboxylic acids of Component (B).
  • the ratio of the charge of Component (A) to that of Component (B) can be adjusted to obtain the viscosity as desired. Furthermore, it is preferable to remove a fraction of light components to perfection, to provide the flash point of 290°C or higher.
  • the thus obtained synthetic esters can be used singly as they are or by mixing them to have the viscosity as desired, to serve as the hydraulic base oil.
  • the synthetic esters to be used as the hydraulic base oil have the kinematic viscosity of 40 to 80cSt, preferably 45 to 65cSt at 40°C. If the viscosity is too high, the low fluidity would result, followed by low efficiency of instruments. If the viscosity is too low, the hydraulic oils are liable to change into a mist and burn when they are erupted. It is preferable that the hydraulic oils have the flash point of 290°C or higher. If the flash point is lower than 290°C, the hydraulic oils are liable to catch fire.
  • the hydraulic oiles have the iodine value of 65 or lower.
  • the oxidative stability can be shown by such iodine value. Therefore, if the value is higher than 65, the hydraulic oiles are liable to have a larger amount of olefin component and shorter oxidation life, and to burn.
  • the flame retardant hydraulic oils of the present invention contain the hydraulic base oils comprising the thus obtained synthetic esters as the essential component. Furthermore, it is preferable that said flame retardant hydraulic oils additionally contain a high-molecular compound having a number average molecular weight of 10,000 to 400,000.
  • a high-molecular compound a polyolefin, a polyacrylate, a polymethacrylate, a polyalkylene glycol, a polyalkylene glycol alkylether, a styrene-olefin copolymer, a styrene-maleic acid ester copolymer, a polyester and the like can be mentioned.
  • the methacrylate-based polymers or the styrene-maleic acid ester copolymers are preferably used.
  • the base oils are made less liable to change into a mist and it is said high-molecular compounds which are added thereto so that the mists of base oils are even harder to develop.
  • their molecular weights are preferably 10,000 to 400,000. If the molecular weight is smaller than this range, said effect can hardly be obtained undesirably If it is larger than the range, the hydraulic oils are undesirably liable to deteriorate due to the shear when they are used, followed by the fadeout of effects and the reduction of viscosity.
  • said high-molecular compounds be contained in the hydraulic oils in a ratio of 0.01 to 2.0% by weight. If the content is smaller than this range, the present invention is hardly effective undesirably If it is larger than the range, the hydraulic oils are more liable to deteriorate due to shear undesirably.
  • the flame retardant hydraulic oils of the present invention may as well be mixed with routinely used lubricating oil additives, such as antioxidant, extreme pressure agent, rust preventives, defoaming agent, demulsifier and the like.
  • antioxidants to be used herein include a phenol-based antioxidant such as 2,6-di-t-butyl-4-methylphenol, 4,4'-methylenebis(2,6-di-t-butyl-4-methylphenol; an amine-based antioxidant such as N-phenyl- ⁇ -naphthylamine, N-phenyl- ⁇ -naphthylamine, phenothiazine and monooctyldiphenylamine; or a sulfur-based antioxidant such as alkyl disulfide and benzothiazole; and a zinc dialkyldithiophosphate.
  • a phenol-based antioxidant such as 2,6-di-t-butyl-4-methylphenol, 4,4'-methylenebis(2,6-di-t-butyl-4-methylphenol
  • an amine-based antioxidant such as N-phenyl- ⁇ -naphthylamine, N-phenyl- ⁇ -naphthylamine, phenothi
  • extreme pressure agent examples include a zinc dialkyldithiophosphate, a dialkylpolysulfide, a triarylphosphate, a trialkylphosphate and the like.
  • Examples of the rust preventives include an alkenyl succinate, a sorbitan monooleate, a pentaerythritol monooleate and an aminephosphate.
  • Examples of the defoaming agent include a dimethylpolysiloxane and a diethylsilicate.
  • Examples of the demulsifier include a polyoxyalkylene glycol, a polyoxyalkylene alkylether, a polyoxyalkylene alkylamide and a polyoxyalkylene fatty acid ester.
  • the flame retardant hydraulic oils of the present invention as obtained above have the biodegradability of 67% or more as the result of the biodegradation test according to the CEC method.
  • the flame retardant hydraulic oils of the present invention are excellent in the flame retardancy, heat stability, oxidative stability and unaccompanied by the dangers of pinhole fire by incorporating the hydraulic base oils which comprise as the essential component the synthetic esters formed by reacting the polyols of Component (A) with the carboxylic acids of Component (B).
  • these flame retardant hydraulic oils can find their application, for example in various hydraulic instruments, construction equipment, injection machines, machine tools, hydraulically driven robots and the like. Furthermore, they can be used as an engine oil, a gear oil, an industrial lubricating oil for other uses and the like.
  • biodegradable capable of finding the application as a lubricating oil preferable from the viewpoint of environmental protection.
  • a Dean and Stark water separator equipped with a stirrer, a thermometer, a argon gas blower and a condenser was joined to a four neck flask having an internal volume of 5 liter.
  • 603g (4.5mole) of a trimethylolpropane, 2,490g (8.8mole) of an oleic acid and 1,340g (4.7mole) of an isostearic acid were charged. Then, the mixture was subjected to the esterification, heated by a mantle heater in a stream of argon.
  • Examples 2 to 4 and Comparative Examples 1 to 4 were carried out by repeating the esterification of Example 1 except that each component was replaced by that listed in Table 1, to prepare each corresponding ester.
  • Example 6 1 TMP (1.0) Oleic acid(2.22) Isostearic acid(0.78) Polymethacrylate
  • Example 7 1 TMP(1.0) Oleic acid(2.22) Isostearic acid(0.78) Styrene-maleic acid ester copolymer
  • Example 8 2 ESG(1.0) Oleic acid(0.4) Isostearic acid(1.6) Polymethacrylate
  • Example 9 2 ESG (1.0) Oleic acid(0.4) Isostearic acid(1.6) Styrene-isoprene copolymer Number average molecular weight Amount of addition (wt.%) Continuous burning time (second)
  • Example 6 140,000 1.1 1 Example 7 300,000 0.4 1
  • Example 8 140,000 1.4 1
  • Example 9 300,000 0.2 2

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Lubricants (AREA)

Claims (10)

  1. Flammbeständiges Hydrauliköl, das ein Hydraulikgrundöl enthält, das im wesentlichen aus einem synthetischen Ester besteht, der ein Produkt ist, das durch Reagieren von (A) mindestens einem Polyol, ausgewählt aus der Gruppe, die aus Neopentylglykol, 2,2-Dimethyl-3-hydroxypropyl-2',2'-dimethyl-3'-hydroxypropionat und Trimethylolpropan besteht, mit (B) einer Carbonsäure, die 15 bis 85 mol-% Oleinsäure, bezogen auf die gesamte Carbonsäure und 15 bis 85 mol-% Isostearinsäure, bezogen auf die gesamte Carbonsäure, umfaßt, erhalten wird, wobei der synthetische Ester eine kinematische Viskosität von 40 bis 80 cSt bei 40°C und einen Flammpunkt von 290°C oder höher besitzt.
  2. Flammbeständiges Hydrauliköl nach Anspruch 1, worin die Carbonsäure der Komponente (B) weiter 70 mol-% oder weniger einer Monocarbonsäure mit 6 bis 22 Kohlenstoffatomen (ausschließlich der Oleinsäure und der Isostearinsäure), bezogen auf die gesamte Carbonsäure, enthält.
  3. Flammbeständiges Hydrauliköl nach Anspruch 1, das eine Iodzahl von 65 oder niedriger besitzt.
  4. Flammbeständiges Hydrauliköl nach Anspruch 1, das weiter 0,01 bis 2,0 Gew.-% einer hochmolekularen Verbindung mit einer massenmittleren Molekülmasse von 10000 bis 400000 enthält.
  5. Flammbeständiges Hydrauliköl nach Anspruch 4, worin die hochmolekulare Verbindung aus der Gruppe ausgewählt wird, die aus Polymeren auf Polymethacrylatbasis und Styrol-Maleinsäureester-Copolymeren besteht.
  6. Flammbeständiges Hydrauliköl nach Anspruch 1, das eine biologische Abbaubarkeit von 67 % oder höher als Ergebnis des biologischen Abbautests entsprechend dem CEC-Verfahren aufweist.
  7. Flammbeständiges Hydrauliköl nach Anspruch 2, das eine biologische Abbaubarkeit von 67 % oder höher als Ergebnis des biologischen Abbautests entsprechend dem CEC-Verfahren aufweist.
  8. Flammbeständiges Hydrauliköl nach Anspruch 3, das eine biologische Abbaubarkeit von 67 % oder höher als Ergebnis des biologischen Abbautests entsprechend dem CEC-Verfahren aufweist.
  9. Flammbeständiges Hydrauliköl nach Anspruch 4, das eine biologische Abbaubarkeit von 67 % oder höher als Ergebnis des biologischen Abbautests entsprechend dem CEC-Verfahren aufweist.
  10. Flammbeständiges Hydrauliköl nach Anspruch 5, das eine biologische Abbaubarkeit von 67 % oder höher als Ergebnis des biologischen Abbautests entsprechend dem CEC-Verfahren aufweist.
EP93119558A 1992-12-07 1993-12-04 Flammfestes Hydrauliköl Expired - Lifetime EP0612831B1 (de)

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EP0612831A1 (de) 1994-08-31
DE69317643D1 (de) 1998-04-30
US6361711B1 (en) 2002-03-26
DE69317643T2 (de) 1998-07-09

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